Ammonia → 8-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithiaoctanoic acid

HRID 22588

反応式

HRID 22588 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30](O)=[O:31])[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C([N:35](CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.N>C(Cl)Cl.CC#N.O>[C:30]([CH2:29][CH2:28][S:27][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH2:12][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:31])[NH2:35]

参加物

7

反応物 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 100513215-(3-(7-Chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithianonanedioic acid

生成物 1

HCID 199305168-Carbamyl-5-(3-(7-chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithiaoctanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 21877088Acetonitrile methylene chloride溶媒

反応条件

温度
0 °C

実験手順

The diacid (Example 3) (3.954 g, 8.04 mmoles) was dissolved in 250 mL CH2Cl2 :CH3CN 4:1. Triethyl amine (2.5 mL, 2.2 equiv.) was added followed, at 0° C., by 2-chloro-1-methylpyridinium iodide (2.257 g, 1.1 equiv.). After stirring 1 hour at 0° C., ammonia was added and the mixture stirred for another hour at 10° C. Water was then added and the aqueous layer acidified to pH 5. Extraction with CH2Cl2 (2×) and EtOAc (2×) and flash chromatography of the residue on silica with acetone: CH2Cl2 :AcOH 40:60:1 and 50:50:1 afforded the title compound.

後処理

  1. stirringthe mixture stirred for another hour at 10° C
  2. extractionExtraction with CH2Cl2 (2×) and EtOAc (2×) and flash chromatography of the residue on silica with acetone: CH2Cl2 :AcOH 40:60:1 and 50:50:1

出典と根拠

ORDレコード
ord-ab2d7542bb27407e9059ce8f02be781c
出典データセット
uspto-grants-1995_06
特許番号
US05428171

関連ノート

読み込み中…